Acetate-hydrochloric acid → 4-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-[5-(4-morpholin-4-yl-phenyl)-1H-imidazol-2-yl]-1H-pyridin-2-one

HRID 2377976Notes

Reaction equation

HRID 2377976 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[N:11](O)[C:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=2)=[CH:13][N:14]=1.[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]([OH:58])[CH2:36][NH:37]C2C=CNC(=O)C=2C2NC(C3C=CC=CC=3)=C(CC)N=2)[CH:32]=[CH:33][CH:34]=1.Cl.C(O)(=O)C>[Cl-].[Ti+3].[Cl-].[Cl-]>[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]([OH:58])[CH2:36][NH:37][C:2]2[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=2[C:10]2[NH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[CH:13][N:14]=2)[CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 22641269Acetate-hydrochloric acidHCID 598575612-(4-Iodo-2-methoxy-pyridin-3-yl)-5-(4-morpholin-4-yl-phenyl)-imidazol-1-olHCID 178437584HCID 178437584, compound

Product 1

HCID 1354059064-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-[5-(4-morpholin-4-yl-phenyl)-1H-imidazol-2-yl]-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 10313229titanium(III) trichlorideCatalyst

Procedure

2-(4-Iodo-2-methoxy-pyridin-3-yl)-5-(4-morpholin-4-yl-phenyl)-imidazol-1-ol (0.049 g, 0.102 mmol) was reacted as described for the synthesis of 4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-3-(4-ethyl-5-phenyl-1H-imidazol-2-yl)-1H-pyridin-2-one except that the compound was first treated with titanium(III) chloride LCMS (+ESI, M+H+) m/z 463) and then hydrochloric acid/acetic acid. The title material was obtained (0.007 g, 14%) as a yellow solid. HPLC 85% (220 nm), LCMS (+ESI, M+H+) m/z 492; 1H NMR (400 MHz, methanol-d4) δ (ppm): 3.18 (4H, br t), 3.65 (1H, br dd), 3.74 (1H, br dd), 3.87 (4H, m), 5.02 (1H, m), 6.26 (1H, d, J=7.5 Hz), 7.02 (2H, d, J=8.6 Hz), 7.22-7.56 (7H, m), 7.74 (1H, d, J=7.9 Hz).

Sources & evidence

ORD record
ord-36795513013a46cca92b71698ac1112d
Source dataset
uspto-grants-2008_12
Patent number
US07470713B2

Reaction notes

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